Rhodium‐Catalyzed Geminal Oxyfluorination and Oxytrifluoro‐Methylation of Diazocarbonyl Compounds |
| |
| Authors: | Dr Weiming Yuan Dr Lars Eriksson Prof Kálmán J Szabó |
| |
| Affiliation: | 1. http://www.organ.su.se/ks/;2. Department of Organic Chemistry, Stockholm University, Sweden;3. Department of Materials and Environmental Chemistry, Stockholm University, Sweden |
| |
| Abstract: | A new reaction for the rhodium‐catalyzed geminal‐difunctionalization‐based fluorination is presented. The substrates are aromatic and aliphatic diazocarbonyl compounds. As the fluorine source a stable and easily accessible benziodoxole reagent was used. A variety of alcohol, phenol, and carboxylic acid reagents were employed to introduce the second functionality. The reaction was extended to trifluoromethylation using a benziodoxolon reagent. The fluorination and trifluoromethylation reactions probably proceed by a rhodium‐containing onium ylide type intermediate, which is trapped by either the F or CF3 electrophiles. |
| |
| Keywords: | diazo compounds fluorine hypervalent compounds reaction mechanisms rhodium catalyst |
|
